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Full text of "Practical Organic Chemistry"

250

PRACTICAL ORGANIC CHEMISTRY

The second yields, in acetic acid solution, formasyl derivatives,
CHUCO.CHo.COOCoH, -t- CrII,N,Cl = CM ..CO CH:N.NH.Q.II

' '                +"co2-!-c2r-isOH +

CH3.CO.CH:N.NriC,5lI5 + C0rir>N2Cl

- ri^T rn r/N:N-cIT     i-

- ^L5.co.c^N<N1LCyIr_ +

Acetyl cliphenyl formnzyl.

The third is capable of the utmost variety, since the sodium
in the sodium compound may be removed by the action of :
i. Iodine,   which  leads  to  the  formation   of   acetosuccinic

ester,

CHo.CO.CHNa.COOCoII,

"   '

CH3.CO.CHNa.COOC.2irs

CH,.CO.CII.COOCJIr

L, =       '        |              ~   '+ 2NaI.

"     CH^.CQ.CII.COOCJL,

Acetosuccinic ester.

2.  Alkyl  iodide,  whereby two  atoms  of hydrogen  may   be
successively replaced by the same or different radicals,

CH.,.CO.CHNa.COOCoH, + CH,I      = CH3.CO.CH(CIL)COOC,I I*

'+ Nal.

CHn.CO.CNa(CFI,}.COOCoII5+ CH3I =CH^CO.C(CIL,).,COOC>I U,

' + Nal.

3.  Acid chloride, which is of similar character to the fore-
going process, but gives rise in some cases to the simultaneous
formation of two isomeric compounds, a fact which at one  time
threw considerable doubt  on  the ketonic character of acelo-
acetic ester.    Thus chloroformic ester and sodium acetoacetic
ester produce the following two derivatives, of which the second
predominates :

CH3.CO.CH(C02C2H5)2.

Acetylmalonic escer.

CHS. C(OC02C2Hs) 'CH. COoC2I I5.

jS-Carboxethylacetoacetic ester.

The synthetic capabilities of this compound are not yet
exhausted. Acetoacetic ester and its alkyl derivatives undergo
decomposition in two ways, according to whether dilute
alkalis and acids or, on the other hand, strong alkalis are
employed.